Methyl-3,4,5-trimethoxy-2-[2-(nicotinamide)benzamido] benzoate - Compound Card

Methyl-3,4,5-trimethoxy-2-[2-(nicotinamide)benzamido] benzoate

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Methyl-3,4,5-trimethoxy-2-[2-(nicotinamide)benzamido] benzoate

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Peptide
Canonical Smiles COC(=O)c1cc(OC)c(c(c1NC(=O)c1ccccc1NC(=O)c1cccnc1)OC)OC
InChI InChI=1S/C24H23N3O7/c1-31-18-12-16(24(30)34-4)19(21(33-3)20(18)32-2)27-23(29)15-9-5-6-10-17(15)26-22(28)14-8-7-11-25-13-14/h5-13H,1-4H3,(H,26,28)(H,27,29)
InChIKey DXZREYMSIRCHNS-UHFFFAOYSA-N
Formula C24H23N3O7
HBA 8
HBD 2
MW 465.46
Rotatable Bonds 8
TPSA 125.08
LogP 3.4
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 465.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178

Showing of synonyms

  • Hamed A, Abdel-Razek A.S, et al. (2020). Terretonin O: a new meroterpenoid from Aspergillus terreus. Nat Prod Res,2020,34(7),965-974. [View] [PubMed]
Pubchem: 12961683
Nmrshiftdb2: 70003107

No compound-protein relationship available.

Structure

SMILES: c1ccccc1NC(=O)c2c(cccc2)NC(=O)c3cccnc3

Level: 2

Mol. Weight: 465.46 g/mol

Structure

SMILES: c1ncccc1C(=O)Nc2ccccc2

Level: 1

Mol. Weight: 465.46 g/mol

Structure

SMILES: c1ccccc1C(=O)Nc2ccccc2

Level: 1

Mol. Weight: 465.46 g/mol

Structure

SMILES: c1ccncc1

Level: 0

Mol. Weight: 465.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 465.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.490
Plasma Protein Binding
61.49
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.350
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.330
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.490
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.010
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-216.480
Rat (Acute)
1.880
Rat (Chronic Oral)
2.900
Fathead Minnow
5.360
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
519.450
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.850
Log(P)
2.99
Log S
-5.17
Log(Vapor Pressure)
-9.29
Melting Point
197.49
pKa Acid
9.0
pKa Basic
4.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9710
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9402
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9299
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.9297
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9279
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9081
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9053
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9024
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8920
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8904
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8876
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8835
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8818
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8798
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8780
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8776
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8625
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8597
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8568
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8539
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8497
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 4 0.8479
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8454
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8405
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8353
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8267
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8237
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8220
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8200
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.8145
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8129
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8095
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8070
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8062
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8018
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.8011
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8000
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7978
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7974
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7947
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7933
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7885
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.7881
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7870
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7845
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7832
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7811
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7788
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7771
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7767
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7761
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7758
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7737
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7726
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7663
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7638
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7629
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7581
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7551
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7547
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7533
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 5 0.7518
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7508
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7452
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7448
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7431
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7419
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7410
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7409
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7387
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7373
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7352
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7351
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7346
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 5 0.7340
Cytochrome P450 2C9 P11712 CP2C9_HUMAN Homo sapiens 3 0.7328
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7320
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7305
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7302
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7299
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7299
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7288
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7279
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7275
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 5 0.7256
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7248
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7244
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7237
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7236
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7230
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7223
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7222
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7215
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7207
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7180
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7175
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7174
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7158
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7156
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7147
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7138
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7124
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7123
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7105
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7099
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7059
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7056
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 5 0.7045
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7039
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7038
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7025
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 2 0.7018
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7017

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